Max-Planck-Institut für Kohlenforschung, 45470 Mülheim/Ruhr, Germany.
Org Lett. 2023 Jul 7;25(26):4903-4907. doi: 10.1021/acs.orglett.3c01720. Epub 2023 Jun 26.
After a recent total synthesis had resolved all issues surrounding the constitution and stereostructure of prorocentin, it was possible to devise a new approach aiming at an improved supply of this scarce marine natural product; this compound is a cometabolite of the prototypical phosphatase inhibitor okadaic acid but still awaits detailed biological profiling. The revised entry starts from 2-deoxy-d-glucose; keys to success were a telescoped hemiacetal reduction/acetal cleavage and an exquisitely selective gold/Brønsted acid-cocatalyzed spiroacetalization.
在最近的一次全合成解决了 prorocentin 的构成和立体结构的所有问题后，人们就有可能设计出一种新的方法，旨在改善这种稀缺海洋天然产物的供应；该化合物是典型磷酸酶抑制剂 okadaic 酸的副产物，但仍有待详细的生物学分析。修订后的路线从 2-脱氧-d-葡萄糖开始；成功的关键是缩合的半缩醛还原/缩醛裂解和高度选择性的金/布朗斯特酸协同螺缩醛化。
